This invention relates to novel 2,5-substituted-cyclohexane-1,4-diones which are of value as starting materials for the production of polyesters, polyamides, polyurethanes, etc. or for the synthesis of 7,7,8,8-tetracyanoquinodimethane (TCNQ) derivatives.
TCNQ occurs as yellow crystals melting at 293.5.degree. to 296.degree. C. This compound is ready to accept one electron to form a stable anion radical and its derivatives show very small electrical resistance values. These compounds are converted to phenylenedimalonitrile on reduction with thiophenol, mercaptoacetic acid, hydrogen iodide or the like, and the latter is reconverted to TCNQ on oxidation with N-bromosuccinimide. Chemical condensers are among the commercial applications of TCNQ.
Since TCNQ is thus electrically conductive despite its being an organic compound, it is rewarding to discover conductive compounds skeletally analogous to TCNQ for the research and development of organic conductive sbbstances and for their commercial implementation.
This invention is predicated on the discovery of a novel compound in the course of synthetic investigation of various TCNQ derivatives promissing as organic semiconductors.